Peter Carlisle

Amid the frenetic summer
of 2004, in which swimmer Michael Phelps would qualify for and then dominate
the Athens Olympic Games, there was a guy in the Phelps entourage accessorized
with a backpack over his shoulder, wraparound shades and shorts, and often wearing
a mild smirk rather than a nervous scowl.

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Was he an obscure member
of the American swim team? A Zen master, dietitian or physical trainer? Try
none of the above. It was in fact Octagon’s Peter Carlisle, Phelps’
lead agent and the firm’s director of Olympics and action sports.

Although at 36 Carlisle
insists he has “aged considerably” since his first time as a Forty
Under 40 honoree, in 2002, the effect so far seems mostly to the upside. Sometimes
a little older means a little bolder. The former corporate lawyer believed in
the late 1990s that a burgeoning generation of radical U.S. winter athletes,
namely snowboarders, was on the verge of fame — and the income to go with
it.

That theory was reality
by 2002, when Octagon athletes Kelly Clark and Ross Powers won gold. And Carlisle
was well past any doubts heading into 2003 that his then-18-year-old swimming
client, Phelps, was destined for historic heights.

“Coming off a history-making
performance by Phelps [five world records] at the 2003 Barcelona World Championships,
Peter had the foresight to propose a contract extension through 2009,”
said marketing vice president Craig Brommers of swimwear maker Speedo.

The most famous element
of that deal was the well-documented $1 million bonus for seven golds. It generated
buzz — a “bonus” for six other sponsors that include Omega watches
and Visa (through 2008) — and linked Phelps to an undisputed Olympic legend,
Mark Spitz. But there was risk. Would Phelps reel from financial and media pressure
with expectations so high?

“We knew there might
be some backlash,” Carlisle said. “[But] it was one of the things
Michael did that made people view swimming differently.”

Carlisle said he never
believed his client was under pressure to earn the million bucks. He had negotiated
a basket of endorsement deals, some into six figures annually, with commitments
in place beyond ’04.

“He had no monetary
pressure on him,” Carlisle said of Phelps, who ultimately won six gold
and a record eight medals overall. “Don’t think he wasn’t incentivized
to win five [gold], four, three, two or one. He had no financial pressure.”

Phelps appeared on 13 magazine
covers and was featured in six nationally televised ad campaigns, and “we
did all of that without materially affecting his training,” said Carlisle,
who’d been warned that even one poor practice session would hurt Phelps’
chances at the Games.

Carlisle’s approach
represents “the epitome of modern representation for an elite athlete,”
said Phil de Picciotto, Octagon’s president of athletes and personalities.
“Peter is very well-equipped to handle the panoply of services required
today. He is very competent and highly collaborative.”